Benjamin Todd Jealous’s decision to resign as president and CEO of the NAACP at the end of this year is a shocking development in the history of the civil rights organization.

Jealous, 40, announced this past weekend in a series of media interviews that effective December 31, he would no longer lead the National Association for the Advancement of Colored People. He said repeatedly that the decision to leave his post midway through an extended, three-year contract with two years remaining stemmed from a desire to spend more time with his family.

“Leadership knows when to step up and when to step down,” he told USA Today in an interview posted Sunday. “This day I can say with pride that I’m prepared to step down and make room for the next person who will lead this organization to its next chapter.”

Jealous made history in the 104-year-old organization when he was selected five years ago, at age 35, as its youngest leader. Now, he’s making it again by becoming the first in recent history to leave voluntarily with his head held high, and to leave the NAACP’s standing in a better and stronger place than when he arrived.

Jealous replaced former Verizon executive Bruce Gordon, who served as NAACP president for two years and signaled a desire by the organization to move in a new direction as it sought to attract younger members and set a new 21st-century agenda.

Prior to Gordon’s selection, the NAACP preferred to choose its top official from the ranks of religious, political, or civil rights leadership. Prominent civil rights activist Roy Wilkins led the NAACP from 1955 to 1977 with virtually unchallenged authority. Rev. Benjamin L. Hooks, a Baptist minister from Tennessee, followed Wilkins as executive director, serving in the role until he retired in 1992.

Over the next decade or so, the NAACP’s top office roiled in scandal. Benjamin F. Chavis, a civil rights activist and minister, led the NAACP from 1993 to 1994. Next in line was former Rep. Kweisi Mfume (D-MD), who headed the Congressional Black Caucus from 1993 to 1995 and then led the NAACP from 1996 to 2004. Both Chavis—now known as Chavis Muhammad—and Mfume left the NAACP amid allegations of sexual misconduct and financial impropriety while serving at the organization’s Baltimore headquarters.

So when Gordon came onboard in 2005, there were high hopes within the NAACP that it could point to his acumen in business to help put the then-recent woes behind the organization. After all, Gordon represented the success of the NAACP’s past campaigns to open up education, jobs, and opportunity. He was the first leader of the NAACP to prove himself in business—or, to put it more bluntly, to reflect success possible for black Americans in the larger white corporate world, which past NAACP victories had made possible.

But Gordon, who was the unanimous choice of the NAACP board, proved to be a poor fit for the organization. He resigned just two years after taking the job, citing conflict with the organization’s unwieldy 64-member board.

I did not step into the role to be a caretaker, to be dictated to. I stepped into the role to understand as best I could the needs of the African American community and then to propose strategies and policies and programs and practices that could improve conditions for African Americans. … The things I had in mind were not consistent with what some—unfortunately, too many—on the board had in mind.

For the most part, Jealous’ success as the NAACP’s leader has helped remove the blotted recent history. He has worked tirelessly at putting forward a younger face and message on behalf of the NAACP. This has been most evident as Jealous was quick to seize upon the Trayvon Martin shooting and trial, making the NAACP a leading voice in the national debate over Florida’s “Stand Your Ground” laws.

His embrace of certain issues, however, has caused some within the NAACP to second-guess him. For example, Jealous’s promotion of a NAACP resolution to embrace same-sex marriage prompted Rev. Keith Ratliff Sr. of Des Moines, Iowa, to resign from the board.

Perhaps Jealous’s most obvious misstep occurred in 2010 when he condemned former Agriculture Department official Shirley Sherrod for making racist remarks and called for her resignation, only to learn later that she hadn’t made the comments and was unjustly fired.

Through it all, however, Jealous’s departure is being lamented, and his tenure in office considered largely successful.

“In the last five years, we’ve had double-digit revenue growth,” Jealous told USA Today last weekend. “We’ve spent five years in the black.” In fact, as the newspaper reported, under Jealous’s leadership, the NAACP’s donor base grew to 132,543 last year from 16,422 in 2007, just before he took over. Similarly, the organization’s revenues increased to $46 million in 2012 from $25.7 million in 2008. Out of a total score of 70, the independent nonprofit charity-reviewing organization Charity Navigator gives the NAACP 51.42 for finances and 70 for accountability and transparency, the newspaper said.

That’s no small accomplishment.

As the news of his impending resignation is still fresh, there’s no obvious choice for his replacement or what lies ahead for him, although Jealous said he plans to help hire the new president. After that, he told USA Today columnist DeWayne Wickham that he’s planning to create a political action group modeled after EMILY’s List for people of color. EMILY’s List is a political fundraising group that seeks to elect pro-choice and Democratic women.

“It’s not altogether clear to me that every candidate to be supported is a Democrat,” Jealous told Wickham. “The fact that civil rights has become a one-party affair is very dangerous to the cause of civil rights.”

As for who will replace him, Jealous hinted at an even more historic move for the NAACP. Could the next face of the old civil rights organization be a woman’s?

Sam Fulwood III is a Senior Fellow at the Center for American Progress and Director of the CAP Leadership Institute. His work with the Center’s Progress 2050 project examines the impact of policies on the nation when there will be no clear racial or ethnic majority by the year 2050.